4-Bromo-2,2'-bipyridine supplier

Name
4-Bromo-2,2''-bipyridine
EINECS
CAS No. 14162-95-9
Article Data22
CAS DataBase
Density 1.494 g/cm³
Solubility
Melting Point 52 °C
Formula C₁₀H₇BrN₂
Boiling Point 325.163 °C at 760 mmHg
Molecular Weight 235.083
Flash Point 150.454 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Bromo-2,2'-bipyridine;4-Bromo-2,2'-bipyridyl;
PSA 25.78000
LogP 2.90610

Synthetic route

: 14163-03-2
4-bromo-2,2’-bipyridine N-oxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With phosphorus tribromide In chloroform at 0 - 60℃; for 2h; Inert atmosphere;	99%
With phosphorus tribromide In chloroform at 0℃; for 5h; Inert atmosphere; Reflux;	98.7%
With phosphorus tribromide In dichloromethane for 4h; Inert atmosphere; Reflux;	94%

: 14163-00-9
4-nitro-2,2'-bipyridine N-oxide

A: 14162-95-9
4-bromo-2,2'-bipyridyl

B: 14163-03-2
4-bromo-2,2’-bipyridine N-oxide

Conditions

Conditions	Yield
With Acetyl bromide; acetic acid for 4h; Inert atmosphere; Reflux;	A 14.6% B 80.3%

: 14163-00-9
4-nitro-2,2'-bipyridine N-oxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With Acetyl bromide; phosphorus tribromide; acetic acid In chloroform	75%
With Acetyl bromide; acetic acid at 130℃; for 2h; Microwave irradiation;	75%
With Acetyl bromide; phosphorus tribromide at 40℃; for 1.25h; Reflux;	56%

: 33421-43-1
2,2'-bipyridyl N-oxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With Acetyl bromide In acetic acid for 24h; Inert atmosphere; Reflux;	68%
Multi-step reaction with 3 steps 1: 49 percent / HNO3; H2SO4 / 31 h / 100 °C 2: acetyl bromide 3: PBr3 View Scheme
Multi-step reaction with 2 steps 1: fuming HNO3, conc. H2SO4 / 3 h / 100 °C 2: 36 percent / AcBr, PPh3 / 2 h / Heating View Scheme

: 249644-59-5
4-bromo-2,2′-bipyridine-1,1′-dioxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With phosphorus tribromide In chloroform for 1.25h; deoxygenation; Heating;	60%

: 4-tributylstannyl-<2,2'>-bipyridine

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With bromine In chloroform at -60℃;	57%

: 30091-53-3
3-(pyridin-2-yl)-1,2,4-triazine

: 994-89-8
tributylethynyltin

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
With bromine 1.) 1,2-dichlorobenzene, 180 deg C, 16 h; 2.) CHCl3, -60 deg C; Yield given. Multistep reaction;

: 366-18-7
[2,2]bipyridinyl

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 13.48 g / magnesium monoperoxyphthalate / ethanol / 5 h / Heating 2: 49 percent / HNO3; H2SO4 / 31 h / 100 °C 3: acetyl bromide 4: PBr3 View Scheme
Multi-step reaction with 3 steps 1: aq. H2O2, AcOH / 12 h / 60 °C 2: fuming HNO3, conc. H2SO4 / 3 h / 100 °C 3: 36 percent / AcBr, PPh3 / 2 h / Heating View Scheme
With hydrogen bromide; dihydrogen peroxide In methanol at 20℃; for 20h;

: 7275-43-6
[2,2']bipyridinyl 1,1'-dioxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 16 percent / KNO3; H2SO4 / 24 h / 100 °C 2: 64 percent / CH3COBr; glacial AcOH / 2 h / Heating 3: 60 percent / PBr3 / CHCl3 / 1.25 h / Heating View Scheme

: 14163-01-0
4-nitro-2,2′-bipyridine N-oxide

: 14162-95-9
4-bromo-2,2'-bipyridyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / CH3COBr; glacial AcOH / 2 h / Heating 2: 60 percent / PBr3 / CHCl3 / 1.25 h / Heating View Scheme

: 17084-13-8
potassium hexafluorophosphate

: {bis(2-(2'-phenylato)pyridine)Cliridium(III)}2

: 14162-95-9
4-bromo-2,2'-bipyridyl

: C32H23BrIrN4(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: {bis(2-(2'-phenylato)pyridine)Cliridium(III)}2; 4-bromo-2,2'-bipyridyl In methanol; dichloromethane for 1.5h; Reflux; Stage #2: potassium hexafluorophosphate In water; acetonitrile	98%

...Expand

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1066-54-2
trimethylsilylacetylene

: 146548-23-4
4-<2-(trimethylsilyl)-1-ethynyl>-2,2'-bipyridine

Conditions

Conditions	Yield
With diisopropylamine; tetrakis(triphenylphosphine) palladium(0)	97%
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene at 80℃;	97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 95℃; for 7h; Inert atmosphere;
Sonogashira Cross-Coupling;
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzine at 80℃;

: 1059575-28-8
2,5-dimethyl-4-trimethylsilyl-1-phenylboronic acid

: 14162-95-9
4-bromo-2,2'-bipyridyl

: C21H24N2Si

Conditions

Conditions	Yield
Stage #1: 2,5-dimethyl-4-trimethylsilyl-1-phenylboronic acid; 4-bromo-2,2'-bipyridyl With sodium carbonate In tetrahydrofuran; water for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 85℃; for 21h; Inert atmosphere;	96%

: ([2,2':5',2''-terthiophen]-3'-ylethynyl)trimethylsilane

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 4-([2,2':5',2''-terthiophen]-3'-ylethynyl)-2,2'-bipyridine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene for 18h; Inert atmosphere; Sealed tube;	95%

: 17084-13-8
potassium hexafluorophosphate

: [Rh2(4-(2-pyridyl)benzaldehyde(-1H))4Cl2]

: 14162-95-9
4-bromo-2,2'-bipyridyl

: C34H23BrN4O2Rh(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: [Rh2(4-(2-pyridyl)benzaldehyde(-1H))4Cl2]; 4-bromo-2,2'-bipyridyl In methanol; dichloromethane for 1.5h; Reflux; Stage #2: potassium hexafluorophosphate In water; acetonitrile	94%

...Expand

: 92-84-2
10H-phenothiazine

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 10-(2,2'-bipyridin-4-yl)-10H-phenothiazine

Conditions

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; potassium tert-butylate In 1,4-dioxane at 110℃; for 18h; Inert atmosphere; Sealed tube;	93%

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 133930-39-9
<2,2';4',4";2",2'">-quaterpyridine

Conditions

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; zinc In N,N-dimethyl-formamide at 20℃; for 10h;	92%
With bis(triphenylphosphine)nickel(II) chloride; zinc In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	92%
With nickel(II) chloride hexahydrate; triphenylphosphine; zinc In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;	19%

: 6165-69-1
Thien-3-ylboronic acid

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 4-(thiophen-3-yl)-2,2'-bipyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; potassium carbonate In water at 150℃; for 2h; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Micellar solution; Microwave irradiation; Green chemistry;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 80℃; for 0.5h; Inert atmosphere; Microwave irradiation;	80%

: 128424-46-4
1,4-diethinyl-2,5-di(octadecyloxy)benzene

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1,4-bis(2',2"-bipyridine-4"-ylethinyl)-2,5-di(octadecyloxy)benzene

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran for 24h; Condensation; Heating;	90%

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 4440-01-1
lithium phenylacetylide

: 444085-26-1
4-(phenylethynyl)-2,2’-bipyridine

Conditions

Conditions	Yield
Stage #1: lithium phenylacetylide With 9-methoxy-9-borabicyclo[3.3.1]nonane In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 4-bromo-2,2'-bipyridyl; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 18h; Suzuki-type coupling; Heating; Further stages.;	90%

: C28H34BNO4

: 14162-95-9
4-bromo-2,2'-bipyridyl

: C32H29N3O2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 85℃; for 23h; Inert atmosphere;	90%

: 14162-95-9
4-bromo-2,2'-bipyridyl

: potassium vinyltrifluoroborate

: 82761-36-2
4-ethynyl-2,2'-bipyridine

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran; water at 85℃; for 48h; Suzuki-Miyayra cross-coupling; Inert atmosphere; Sealed tube;	89%

: 381218-96-8
4′-(4-boronatophenyl)-2,2′:6′,2′′-terpyridine

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 4′-(2,2′-bipyridin-4-yl)-2,2′:6′-2′′-terpyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 20℃; Suzuki Coupling; Inert atmosphere; Reflux; Schlenk technique;	89%

: 14220-21-4
rhenium(I) pentacarbonyl bromide

: 14162-95-9
4-bromo-2,2'-bipyridyl

: facial-bromotricarbonyl(4-bromo-2,2'-bipyridine)rhenium(I)

Conditions

Conditions	Yield
In toluene for 2h; Reflux; Inert atmosphere;	86%

: 950761-81-6
4,4,5,5-tetramethyl-2-(perylene-3-yl)-1,3,2-dioxaborolane

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1456736-21-2
3-(2,2’-bipyridine-4-yl)perylene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85 - 100℃; for 22.33h; Suzuki-Miyaura Coupling; Inert atmosphere;	85.9%

: 437707-60-3
ethyl 3,5-diethynylbenzoate

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1392217-94-5
ethyl 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; triethylamine; triphenylphosphine at 70℃; for 48h; Inert atmosphere;	85%

: 87199-17-5
4-formylphenylboronic acid,

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 4-(2,2'-bipyridyl-4-yl)benzaldehyde

Conditions

Conditions	Yield
With 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate In 1,4-dioxane; water for 6h; Suzuki-Miyaura Coupling; Reflux;	85%

: ruthenium trichloride hydrate

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1228182-23-7
[RuCl2(4-bromo-2,2'-bipyridine)2]

Conditions

Conditions	Yield
With glucose; L-ascorbic acid In ethane-1,2-diol; H2O Ar; Ru compd. (7.3 mmol) heated at 80°C for 15 min in EG/H2O mixt. (3/1 v/v), ligand (14.4 mmol) added, heated at 100°C, glucose (1.1 mmol) added, stirred for 10 min, L-ascorbic acid (2.8 mmol) added, stirred for 30 min; cooled to 0°C, ppt. filtered off, washed (ether/acetone=4/1, ether);	84%

: 1692-15-5
4-pyridylboronic acid

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1148-79-4
2,2':6,2''-terpyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane for 96h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Reflux;	82.9%

: 14162-95-9
4-bromo-2,2'-bipyridyl

: (Sa)-2-(2,2'-bis(methoxymethoxy)-3'-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)-1,1'-binaphthyl-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: (S)-3,3'-bis(2,2'-bipyridin-4-yl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl

Conditions

Conditions	Yield
Stage #1: 4-bromo-2,2'-bipyridyl With tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (Sa)-2-(2,2'-bis(methoxymethoxy)-3'-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)-1,1'-binaphthyl-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium carbonate In toluene for 72h; Inert atmosphere; Reflux;	82%

: 146548-24-5
4′-ethynyl-2,2′-bipyridine

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 146548-30-3
bis(2,2'-bipyridin-4-yl)ethyne

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In benzene at 80℃;	80%
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene at 80℃;	80%

: 101-70-2
bis(4-methoxyphenyl)amine

: 14162-95-9
4-bromo-2,2'-bipyridyl

: C24H21N3O2

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 140℃; for 48h; Inert atmosphere;	80%

: 345911-20-8, 19542-80-4, 158060-65-2, 34795-02-3, 15746-57-3
cis-dichlorobis(2,2′-bipyridine)ruthenium(II)

: ammonium hexafluorophosphate

: 14162-95-9
4-bromo-2,2'-bipyridyl

: rac-[Ru(4-Br-2,2’-bipyridine)(2,2’-bipyridine)2](PF6)2

Conditions

Conditions	Yield
Stage #1: cis-dichlorobis(2,2′-bipyridine)ruthenium(II); 4-bromo-2,2'-bipyridyl In ethanol; water for 4h; Reflux; Stage #2: ammonium hexafluorophosphate In water at 0℃; for 1h; Saturated solution;	80%

...Expand

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 146581-82-0
2,2'-bipyridine-4-carboxaldehyde

Conditions

Conditions	Yield
Stage #1: 4-bromo-2,2'-bipyridyl With n-butyllithium In diethyl ether; hexane; toluene at -78℃; for 1.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane; toluene at -78℃; for 1.5h; Inert atmosphere;	80%

: 955405-38-6, 260441-99-4, 260442-17-9
(rac)-3,3'-bis(pinacolboryl)-2,2'-bis(methoxymethoxy)-1,1'-binaphhyl

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 1269460-56-1, 1246528-38-0, 1257519-10-0
((C10H5)(OCH2OCH3)(C5H3N)(C5H4N))2

Conditions

Conditions	Yield
Stage #1: 4-bromo-2,2'-bipyridyl With tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (rac)-3,3'-bis(pinacolboryl)-2,2'-bis(methoxymethoxy)-1,1'-binaphhyl With sodium carbonate In toluene for 72h; Suzuki coupling; Inert atmosphere; Reflux;	79%

: ammonium hexafluorophosphate

: 178212-01-6
mer-Re(CO)3(PEt3)2Br

: 14162-95-9
4-bromo-2,2'-bipyridyl

: [Re(4-bromo-2,2'-bipyridine)(CO)2(PEt3)2](PF6)

Conditions

Conditions	Yield
Stage #1: mer-Re(CO)3(PEt3)2Br With silver trifluoromethanesulfonate In tetrahydrofuran for 3h; Reflux; Inert atmosphere; Stage #2: 4-bromo-2,2'-bipyridyl In toluene at 90℃; for 36h; Heating; Inert atmosphere; Stage #3: ammonium hexafluorophosphate In methanol	77%

...Expand

: 149817-60-7
4'-ethynyl-2,2':6',6-terpyridine

: 14162-95-9
4-bromo-2,2'-bipyridyl

: 146548-34-7
4'-(2,2'-bipyridin-4-ylethynyl)-2,2':6',2''-terpyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene at 80℃; for 22h;	75%

4-Bromo-2,2'-bipyridine Specification

This chemical is called 2,2'-Bipyridine, 4-bromo-, and its systematic name is 4-bromo-2,2'-bipyridine. With the molecular formula of C₁₀H₇BrN₂, its molecular weight is 235.08. The CAS registry number of this chemical is 14162-95-9. Additionally, its product category is Pharmacetical.

Other characteristics of the 2,2'-Bipyridine, 4-bromo- can be summarised as followings: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 19; (6)ACD/BCF (pH 7.4): 20; (7)ACD/KOC (pH 5.5): 289; (8)ACD/KOC (pH 7.4): 293; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 25.78 Å²; (13)Index of Refraction: 1.612; (14)Molar Refractivity: 54.717 cm³; (15)Molar Volume: 157.35 cm³; (16)Polarizability: 21.692×10^-24cm³; (17)Surface Tension: 50.482 dyne/cm; (18)Density: 1.494 g/cm³; (19)Flash Point: 150.454 °C; (20)Enthalpy of Vaporization: 54.471 kJ/mol; (21)Boiling Point: 325.163 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: Brc1ccnc(c1)c2ncccc2
2.InChI: InChI=1/C10H7BrN2/c11-8-4-6-13-10(7-8)9-3-1-2-5-12-9/h1-7H
3.InChIKey: SCOXFIBXWCCICG-UHFFFAOYAB

Product Name

4-Bromo-2,2''-bipyridine

Synthetic route

4-Bromo-2,2'-bipyridine Specification

Related Products

Hot Products